Water → (1S,2S)-1-(4-benzyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol

Participants

Reaction Conditions

Reaction Steps

Over 20 minutes, (2S)-1-(4-benzyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanone (75 g, 0.18 mol) was added to a suspension of lithium borohydride (3.15 g, 0.15 mol) in ethanol (0.75 L) maintained under a nitrogen atmosphere at 20 to 25° C. After stirring for about 5 minutes, a mild exotherm occurred raising the temperature to 27° C. The slurry was stirred for 42 hours at 20 to 25° C. when HPLC indicated that the reaction was complete. Water (37.5 mL) was added and the slurry was granulated for 1 hour at 20 to 25° C. The white solid was filtered and then washed with ethanol (75 mL), water (150 mL), and finally ethanol (75 mL). The product was dried in vacuo at 40 to 45° C. for 20 hours to give 65.3 g of the title compound. The (1S,2S) amino alcohol product was obtained in 78.3% yield and contained only 2.3% of diastereomers. M.p. 158-161° C., [α]D25+38.7 (c 6.1, CH3OH)

Provenance & Evidence